Immobilized cyclic imide catalyst and process for oxidation of organic compounds with the same

Abstract

To provide a solid catalyst containing a cyclic imide skeleton which is easily available and easily separable from reaction products and which is easily recovered and regenerated, and free from reaction inhibitory factors; and a process for oxidation of organic compounds with the solid catalyst. An immobilized cyclic imide catalyst having a structure represented by following Formula (1), wherein X is oxygen or an —OR group (wherein R is hydrogen atom or a hydroxyl-protecting group); n is 0 or 1; Z 1 is a five- or six-membered cyclic imide skeleton to which an aromatic or nonaromatic ring Z 2 may be adjacent; elliptically shaped moiety S is an inorganic support; A 1 is a group linking silicon atom with the cyclic imide skeleton Z 1 or with the ring Z 2 and is either a divalent hydrocarbon group or a group composed of a divalent hydrocarbon group and an amide bond (—NHCO—); and the cyclic imide skeleton Z 1 and the ring Z 2 may each be substituted.

1 . An immobilized cyclic imide catalyst, having a structure represented by following Formula (1): 
       
         
           
           
               
               
           
         
         wherein X represents oxygen atom or an —OR group, wherein R represents hydrogen atom or a hydroxyl-protecting group; “n” represents 0 or 1; Z 1  represents a five- or six-membered cyclic imide skeleton to which an aromatic or nonaromatic ring Z 2  may be adjacent; elliptically shaped moiety “S” represents an inorganic support; A 1  represents a linkage group linking the inorganic support S with the cyclic imide skeleton Z 1  or with the ring Z 2  and is either a bivalent hydrocarbon group or a group composed of a bivalent hydrocarbon group and an amide bond (—NHCO—); the cyclic imide skeleton Z 1  and the ring Z 2  may each be substituted; and the structure may have, per molecule, two or more of the cyclic imide skeleton Z 1  to which the ring Z 2  may be adjacent. 
       
     
     
         2 . The immobilized cyclic imide catalyst of  claim 1 , wherein, in Formula (1), (i) “n” is 0 and the ring Z 2  is a six-membered aromatic or nonaromatic carbon ring possessing one side in common with the cyclic imide skeleton Z 1 , or (ii) “n” is 1 and the ring Z 2  is naphthalene ring or decahydronaphthalene ring possessing two sides in common with the cyclic imide skeleton Z 1 . 
     
     
         3 . The immobilized cyclic imide catalyst of  claim 1 , wherein the inorganic support S comprises at least one member selected from the group consisting of a silica, an alumina, a titania, a zirconia and a ceria, or comprises a composite oxide of two or more elements selected from the group consisting of silicon, aluminum, zirconium and cerium. 
     
     
         4 . A process for the oxidation of an organic compound, the process comprising the step of carrying out an oxidation reaction of the organic compound in the presence of the immobilized cyclic imide catalyst according to any one of  claims 1  to  3 . 
     
     
         5 . The process for the oxidation of an organic compound of  claim 4 , wherein the oxidation reaction is carried out in a fluidized bed system or fixed bed system. 
     
     
         6 . The process for the oxidation of an organic compound of  claim 4 , wherein a hydrocarbon is oxidized into at least one compound selected from the group consisting of a hydroperoxide, an alcohol, a carbonyl compound and a carboxylic acid.